Enantioselective synthesis of alkenyl aziridine carboxylates and 4-phenylsulfenyl prolines

Chiral cyclic and acyclic allyl aminosulfoxonium ylides have been generated from aminosulfoxonium-substituted gamma,delta-unsaturated alpha-amino acids (method A) and 1-alkenyl aminosulfoxonium salts (method B) upon treatment with DBU. Their application to the asymmetric aziridination of N-tert-butyl-sulfonyl imino ester, generated either in situ (method A) or externally added (method B), gave the corresponding alkenyl aziridine carboxylates with medium to high diastereoselectivity and enantioselectivity. A highly stereoselective Pd(0)-catalyzed isomerization of an E,trans-configured alkenyl aziridine methanol derivative to its E-cis-isomer is described, which proceeded with retention of the double bond configuration. The Michael addition of thiophenol to aminosulfoxonium-substituted gamma,delta-unsaturated alpha-amino acids favours from Re-face. The resulted sulfides were applied to synthesize 4-phenylsulfenyl proline derivatives in overall good yields.

Grantor dc:publisher

Publikationsserver der RWTH Aachen University

Year dc:date

2008

Author dc:creator

• Iska, Vijaya Bhaskara Reddy

Contributors dc:contributor

• Gais, Hans-Joachim

• info:eu-repo/classification/ddc/540
• Asymmetrische Synthese
• Chemie
• Enantioselective synthesis
• Alkenyl Aziridinecarboxylates
• Proline

Statement dc:rights

• info:eu-repo/semantics/openAccess

Language dc:language

eng

Identifier

https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-112707%22

OAI record oai:identifier

https://publications.rwth-aachen.de/oai2d?verb=GetRecord&metadataPrefix=oai_dc&identifier=oai%3Apublications.rwth-aachen.de%3A50152